CN108884055B - Pyridazinone compound or salt thereof, and herbicide containing same - Google Patents

Pyridazinone compound or salt thereof, and herbicide containing same Download PDF

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CN108884055B
CN108884055B CN201780021103.8A CN201780021103A CN108884055B CN 108884055 B CN108884055 B CN 108884055B CN 201780021103 A CN201780021103 A CN 201780021103A CN 108884055 B CN108884055 B CN 108884055B
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pyrazolopyrimidinyl
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CN108884055A (en
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植木寿彦
山田龙
田中久树
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Ishihara Sangyo Kaisha Ltd
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
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    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D513/04—Ortho-condensed systems

Abstract

The present invention provides a novel herbicide that exhibits significant herbicidal activity against undesirable plants. A pyridazinone compound represented by the general formula (I) wherein X is-O-, -S-, -SO-, -SO or a salt thereof2-or-n (y) -; q is a monocyclic aryl group which may have a Z substituent, a monocyclic heteroaryl group which may have a Z substituent, or the like; y is a hydrogen atom or an alkyl group; z is halogen, alkyl, etc.; r1Alkyl, alkenyl, etc.; r is2Hydrogen atom, alkyl group, etc.; r is3Halogen, hydroxy, etc.; r4Hydrogen atom, alkyl group, etc.; n is an integer of 0 to 4).

Description

Pyridazinone compound or salt thereof, and herbicide containing same
Technical Field
The present invention relates to a pyridazinone compound or a salt thereof, and more particularly, to a novel pyridazinone compound or a salt thereof useful as an active ingredient of a herbicide, and a herbicide containing the same.
Background
Patent document 1 describes a pyridazinone compound having a certain chemical structure. The compound has-O-A group at the 4-position of A benzene ring substituted on A pyridazinone ring, and the chemical structure of the compound is different from that of the compound.
Patent document 2 describes a heteroaromatic ring compound having a certain chemical structure. A substituent in a meta position of the phenyl ring in which the pyridine ring is bonded via L1 (substituent R in patent document 2)3And R4) There is no pyridazinone ring, and is distinguished from the compounds of the present invention.
Patent document 3 describes a pyridazinone compound having a certain chemical structure. The compound has a phenyl group or a heteroaromatic ring group directly bonded to a substituent G (benzene ring) of a pyridazinone ring, and the chemical structure is different from that of the compound of the present invention.
Patent document 4 describes a pyridazinone compound having a certain chemical structure. In this compound, a substituent corresponding to the substituent Q in the general formula (I) described later in the present application (substituent R in patent document 4)1) Is NR10R11A group or a heterocycloalkyl ring group, which is chemically different from the compounds of the present invention.
Documents of the prior art
Patent literature
Patent document 1: international publication No. WO2014/119770
Patent document 2: international publication No. WO2014/207601
Patent document 3: international publication No. WO2009/086041
Patent document 4: international publication No. WO2008/013838
Disclosure of Invention
Problems to be solved by the invention
The subject of the invention is: to save labor for weed control and improve productivity of agricultural and horticultural use products, a herbicide exhibiting excellent herbicidal performance against weeds has been discovered.
Means for solving the problems
The present inventors have conducted various studies to solve the above problems and found that pyridazinone compounds having specific chemical structures exhibit high herbicidal effects against various weeds at low doses, thereby completing the present invention.
That is, the present invention relates to a pyridazinone compound represented by the general formula (I) or a salt thereof.
Figure BDA0001815266310000021
(in the formula, wherein,
x is-O-, -S-, -SO2-or-n (y) -;
q is a monocyclic aryl group which may have a Z substituent, a monocyclic heteroaryl group which may have a Z substituent, a bicyclic aryl group which may have a Z substituent, or a bicyclic heteroaryl group which may have a Z substituent;
y is a hydrogen atom or an alkyl group;
R1is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, monocyclic aryl which may have a Z substituent, monocyclic arylalkyl which may have a Z substituent, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dialkylaminoalkyl, alkoxyalkyl, amino, nitro, alkylcarbonylalkyl, alkoxycarbonylalkyl or hydroxycarbonylalkyl;
R2is hydrogen atom, alkyl, haloalkyl, cycloalkyl, halogen, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cyano;
R3is halogen, hydroxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, nitro, amino, alkylcarbonyl or cycloalkyl;
R4is a hydrogen atom, an alkyl group, -C (O) R6、-C(S)R6、-SR7、-SOR7、-SO2R7Monocyclic arylalkyl group which may have Z substituent, alkoxyalkyl group, -CH (J)1)OCOOJ2Alkylcarbonylalkyl, monocyclic aryl which may have a Z substituent, monocyclic arylcarbonylalkyl which may have a Z substituent, alkenyl, alkoxyalkoxyalkyl, alkoxycarbonylalkyl, alkynyl, cyanoalkyl, haloalkoxyalkyl or dialkylaminoalkyl;
R6is alkyl, alkoxy, morpholino (limited to the 4-position), dialkylamino, (monocyclic aryl which may have a Z substituent) (alkyl) amino, cycloalkyl, alkoxyalkyl, alkylthioalkyl, haloalkyl, alkylthio, alkenyl, alkynyl, alkoxycarbonylalkyl, cycloalkylalkyl, cyanoalkyl, alkoxyalkoxyalkyl, monocyclic aryl which may have a Z substituent, monocyclic heteroaryl which may have a Z substituent, monocyclic arylalkyl which may have a Z substituent, monocyclic aryloxyalkyl which may have a Z substituentA group, a monocyclic arylthio group which may have a Z substituent, a monocyclic aryloxyalkyl group which may have a Z substituent, a monocyclic arylthioalkyl group which may have a Z substituent, an alkoxycarbonyl group, an alkoxyalkoxy group, a haloalkoxy group, a haloalkoxyalkoxy group, an alkylthioalkoxy group, a cycloalkoxyalkoxy group, a monocyclic arylalkoxy group which may have a Z substituent, a monocyclic aryloxyalkoxy group which may have a Z substituent, monocyclic heteroaryloxyalkoxy, alkenyloxyalkoxy, alkoxyalkoxyalkoxyalkoxy, alkynyloxy, alkenyloxy, haloalkenyl, dialkylaminoalkyl, alkylthioalkoxy, cycloalkylalkoxy, cycloalkylalkoxyalkoxy, monocyclic arylalkoxyalkoxy which may have a Z substituent, monocyclic heteroarylalkoxyalkoxy which may have a Z substituent, or cycloalkoxy which may have a Z substituent;
R7is an alkyl group, a haloalkyl group, a cycloalkyl group or a monocyclic aryl group which may have a Z substituent;
z is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, cyano, nitro, -C (O) OR5Formyl, alkylthio, alkylsulfinyl, alkylsulfonyl, -CH-NOJ3Or a dialkylaminocarbonyl group;
R5is a hydrogen atom or an alkyl group;
J1is a hydrogen atom or an alkyl group;
J2is alkyl or cycloalkyl;
J3is a hydrogen atom, an alkylcarbonyl group or an alkoxyalkyl group;
n is an integer of 0 to 4)
The present invention is preferably a pyridazinone compound represented by the general formula (I) or a salt thereof.
Figure BDA0001815266310000041
(in the formula (I), the compound (I),
x is-O-, -S-, -SO2-or-n (y) -;
q is a monocyclic aryl group which may have a Z substituent, a monocyclic heteroaryl group which may have a Z substituent, a bicyclic aryl group which may have a Z substituent, or a bicyclic heteroaryl group which may have a Z substituent;
y is a hydrogen atom or an alkyl group;
z is halogen, alkyl, haloalkyl, cyano, nitro OR-C (O) OR5；
R1Is alkyl, alkenyl, alkynyl or cycloalkyl;
R2is a hydrogen atom, an alkyl group, a haloalkyl group or a cycloalkyl group;
R3is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy or cycloalkyl;
R4is a hydrogen atom, an alkyl group, -C (O) R6or-SO2R7；
R5Is a hydrogen atom or an alkyl group;
R6is alkyl, alkoxy or morpholino;
R7is an alkyl group;
n is an integer of 1 to 4)
The present invention also relates to a pyridazinone compound of the above general formula (I) or a salt thereof, a herbicide containing the same as an active ingredient, and a method for controlling undesired plants or inhibiting their growth by applying a herbicidally effective amount of the compound or the salt thereof to the undesired plants or to a place where they grow.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the pyridazinone compound of the general formula (I) or a salt thereof of the present invention, a remarkable improvement in herbicidal activity against undesirable plants (weeds) can be achieved as compared with similar conventional compounds.
Detailed Description
Examples of the halogen atom or the halogen atom as a substituent in the general formula (I) include fluorine, chlorine, bromine, and iodine atoms. The number of halogen atoms as substituents may be 1 or 2 or more, and when the number is 2 or more, each halogen atom may be the same or different. Further, the substitution position of the halogen atom may be an optional position.
Examples of the alkyl group or alkyl moiety in the general formula (I) include straight-chain or branched C groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl groups1-C12A group of (1).
Examples of the alkoxy group or alkoxy moiety in the general formula (I) include straight-chain or branched-chain C groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy groups1-C12A group of (1).
Examples of the alkenyl group or alkenyl moiety in the general formula (I) include straight-chain or branched C-butene groups such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-hexenyl, and 2, 3-dimethyl-2-butenyl2-C6A group of (1).
Examples of the alkynyl group or alkynyl moiety in the general formula (I) include straight-chain or branched C-chain alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl2-C6A group of (1).
Examples of the cycloalkyl group or cycloalkyl moiety in the general formula (I) include C such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl3-C7A group of (1).
Examples of the cycloalkoxy group or cycloalkoxy moiety in the general formula (I) include C such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy3-C7A group of (1).
Examples of the monocyclic aryl group in the general formula (I) include a phenyl group. Examples of the monocyclic heteroaryl group include a 3-to 6-membered heteroaryl group containing 1 to 4O, S or N, and specific examples thereof include a thienyl group, a furyl group, a pyrrolyl group,
Figure BDA0001815266310000061
Azolyl radical, iso-acyl
Figure BDA0001815266310000062
Azolyl radical, iso
Figure BDA0001815266310000063
Azolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-
Figure BDA0001815266310000064
Oxadiazolyl, 1,2,4-
Figure BDA0001815266310000065
Oxadiazolyl, 1,3, 4-thiadiazolyl, 1,2, 4-triazolyl, 1,2, 3-thiadiazolyl, 1,2,3, 4-tetrazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, imidazolinyl, imidazolidinyl, pyrazolinyl, pyrazolidinyl, and the like.
Examples of the bicyclic aryl group in the general formula (I) include naphthyl and indenyl. Furthermore, examples of the bicyclic heteroaryl group include a fused heteroaryl group of a 5-to 6-membered heterocyclic ring containing 1 to 2O, S or N and a benzene ring, and specific examples thereof include a benzothienyl group, a benzofuranyl group, an indolyl group, a benzothiazolyl group, a benzimidazolyl group, and a benzisoxazolyl group
Figure BDA0001815266310000066
Azolyl, benzisothiazolyl, indazolyl, benzoazolyl
Figure BDA0001815266310000067
Azolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazineA group selected from the group consisting of a cinnolinyl group, a quinazolinyl group, a naphthyridinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, an imidazopyridinyl group, a thiazopyridinyl group, a pyrazolopyrimidyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, a triazolopyridinyl group, a pyrazinopyrazinyl group, a pyrazinopyridazinyl group, a pyrimidopyridazinyl group, a pyrimidopyrimidinyl group, a pyridopyridazinyl group, a pyrrolopyridinyl group, a thienopyridinyl group, a naphthyridinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyridopyridinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyridopyridinyl group, a,
Figure BDA0001815266310000068
Azolopyridinyl, pyrazolopyridinyl, iso-pyridinyl
Figure BDA0001815266310000069
Azolopyridinyl, isothiazolopyridinyl, pyrrolopyrimidinyl, thienopyrimidinyl, imidazopyrimidinyl,
Figure BDA00018152663100000610
Azolopyrimidinyl, thiazolopyrimidinyl, iso-pyrimidinyl
Figure BDA00018152663100000611
Oxazolopyrimidinyl, isothiazolopyrimidinyl, pyrrolopyrazinyl, thienopyrazinyl, pyrazolopyridinyl, pyrazolopyrimidinyl and pyrazolopyrimidinyl,
Figure BDA00018152663100000612
Azolopyrazinyl, thiazolopyrazinyl, pyrazopyrazinyl, isoxazolo-pyrazinyl
Figure BDA00018152663100000613
Azolopyrazinyl, isothiazolopyrazinyl, pyrrolopyridazinyl, thienopyridazinyl, pyrrolopyrazinyl, isothiazolopyridazinyl, pyrrolopyridazinyl, pyrrolopyrazinyl, thiazolopyridazinyl, and thiazolopyridazinyl,
Figure BDA00018152663100000614
Azolopyridazinyl, thiazolopyridazinyl, pyrazolopyridazinyl, isoxazinyl
Figure BDA00018152663100000615
Oxazolopyridazinyl, isothiazolopyridazinyl, purinyl, pteridinyl and the like.
The phrase "may have a Z substituent" in the general formula (I) means that the number of Z substituents may be 1 or 2 or more in the case of having a Z substituent, and that each substituent may be the same or different in the case of having a number of Z substituents of 2 or more. Further, the substitution position of each substituent may be an optional position.
The salt of the pyridazinone compound of the formula (I) includes all salts as long as they are agriculturally acceptable, and examples thereof include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as magnesium salts and calcium salts; amine salts such as dimethylamine salt and triethylamine salt; inorganic acid salts such as hydrochloride, perchlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.
In the pyridazinone compound of the formula (I), diastereoisomers and optical isomers may exist, and both isomers and isomer mixtures are included in the present invention. In the present specification, unless otherwise specified, isomers are described as a mixture. In the present invention, various isomers other than the above-mentioned isomers are also included within the scope of the common technical knowledge in the technical field. Furthermore, depending on the kind of isomer, the chemical structure may be different from that of the above general formula (I), but it is obvious that those skilled in the art can sufficiently recognize that these chemical structures are in an isomer relationship with the general formula (I), and therefore, the present invention is within the scope thereof.
The pyridazinone compound of the general formula (I) or a salt thereof (hereinafter referred to as the compound of the present invention) can be produced by the following production method, a general method for producing a salt or a synthetic example described later, but the method for obtaining the compound of the present invention is not limited to these methods.
[ production method 1]
The compound of formula (I-1) which is a compound of the present invention can be produced by reacting a compound of formula (I-2) with a compound of formula (II) in the presence of a base.
Figure BDA0001815266310000071
In the formula, T is each atom of chlorine, bromine or iodine, R4aIs alkyl, -C (O) R6、-C(S)R6、-SR7、 -SOR7、-SO2R7Monocyclic arylalkyl group which may have Z substituent, alkoxyalkyl group, -CH (J)1)OCOOJ2An alkylcarbonylalkyl group, a monocyclic aryl group which may have a Z substituent, a monocyclic arylcarbonylalkyl group which may have a Z substituent, an alkenyl group, an alkoxyalkoxyalkyl group, an alkoxycarbonylalkyl group, an alkynyl group, a cyanoalkyl group, a haloalkoxyalkyl group or a dialkylaminoalkyl group, X, Q, R1、R2、R3、R6、R7、Z、J1、J2And n is as described above.
Examples of the base used in the present reaction include organic bases such as triethylamine and pyridine. The amount of the base used is usually 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of the formula (I-2).
The reaction is generally carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inactive to the reaction, and examples thereof include diethyl ether and di-n-ethyl ether
Figure BDA0001815266310000081
Ethers such as alkane, Tetrahydrofuran (THF) and dimethoxyethane, or a mixed solvent thereof.
The amount of the compound of formula (II) used in the present reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (I-2).
The reaction temperature of the reaction is usually-30 to 180 ℃, and preferably-10 to 80 ℃. The reaction time of this reaction is usually 10 minutes to 30 hours.
In this reaction, a mixture of the compound of the formula (I-1) and the compound of the formula (E) as an isomer thereof is produced. The compound of formula (I-1) can be isolated by, for example, mixing the reaction mixture obtained by the present reaction with water, extracting with an organic solvent, drying and concentrating the obtained organic layer, and then purifying by silica gel column chromatography.
The compound of formula (II) is a known compound, or can be produced from a known compound by a known method.
[ production method 2]
The compound of formula (I-2) which is a compound of the present invention can be produced by reacting a compound represented by formula (I-3) with morpholine.
Figure BDA0001815266310000091
In the formula, R8Is alkyl or monocyclic arylalkyl which may have a Z substituent, e.g. C1-3Alkyl or benzyl etc., X, Q, R1、R2、R3Z and n are as described above.
The amount of morpholine used in the present reaction is usually 1 to 20 molar equivalents relative to the compound of formula (I-3).
The reaction temperature of the reaction is usually 30 to 180 ℃, preferably 50 to 130 ℃. The reaction time of this reaction is usually 10 minutes to 30 hours.
In addition, the reaction may be carried out by microwave irradiation, and in this case, the reaction may be accelerated.
After the completion of the reaction, for example, the compound of formula (I-2) can be isolated by mixing the reaction mixture with water, adding an acid to make the mixture acidic, extracting the mixture with an organic solvent, drying and concentrating the obtained organic layer, and purifying the organic layer by silica gel column chromatography or the like.
The compound of the formula (I-2) can be produced, for example, by the methods described in heterocycles, 26, pages 1 to 4 (1987), etc., or by methods based thereon.
[ production method 3]
The compound of formula (I-3) as the compound of the present invention can be produced by reacting a compound of formula (III) with a compound of formula (IV) in the presence of a base or a catalyst.
Figure BDA0001815266310000092
In the formula, X, Q, R1、R2、R3、R8T and n are as described above.
Examples of the base used in the present reaction include metal alkoxides such as potassium tert-butoxide; inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride. The amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (III).
Examples of the catalyst used in the present reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, and [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium; copper catalysts such as copper chloride and copper iodide. The amount of the catalyst to be used is usually 0.001 to 0.5 molar equivalent, preferably 0.01 to 0.2 molar equivalent, relative to the compound of the formula (IV).
The reaction is generally carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inactive to the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; diethyl ether, di
Figure BDA0001815266310000101
Ethers such as alkane, THF, dimethoxyethane and the like; amides such as Dimethylformamide (DMF); sulfoxides such as dimethylene sulfone (DMSO); nitriles such as acetonitrile; ketones such as acetone; or a mixed solvent thereof.
The amount of the compound of formula (IV) used in the present reaction is usually 0.5 to 3 molar equivalents, preferably 1 to 2 molar equivalents, relative to the compound of formula (III).
The reaction temperature of the reaction is usually 0 to 200 ℃, preferably 20 to 100 ℃. The reaction time of this reaction is usually 10 minutes to 30 hours.
After the completion of the reaction, for example, the compound of formula (I-3) can be isolated by adding an acid to the reaction mixture to neutralize it, mixing it with water, extracting it with an organic solvent, drying and concentrating the obtained organic layer, and purifying it by silica gel column chromatography.
The compound of formula (IV) is a known compound, or can be produced from a known compound by a known method.
[ production method 4]
The compound of formula (III) can be produced by reacting the compound of formula (V) with an acid.
Figure BDA0001815266310000111
In the formula, R9Is a monocyclic arylalkyl group which may have a Z substituent, e.g. benzyl or 4-methoxybenzyl, etc., X, R1、R2、R3、R8Z and n are as described above.
Examples of the acid used in the present reaction include trifluoroacetic acid. The amount of the acid used is usually 1 to 20 molar equivalents relative to the compound of the formula (V).
The reaction is carried out in the presence of a solvent as required. The solvent is not particularly limited as long as it is inactive to the reaction, and examples thereof include organic acids such as acetic acid and propionic acid; water; or a mixed solvent thereof.
The reaction temperature of the reaction is usually 30 to 180 ℃, preferably 50 to 130 ℃. The reaction time of this reaction is usually 10 minutes to 30 hours.
After the completion of the reaction, the compound of formula (III) can be isolated by, for example, mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the obtained organic layer, and purifying by silica gel column chromatography.
[ production method 5]
The compound of the formula (V) can be produced by reacting a compound represented by the formula (VI) with a compound represented by the formula (VII) or the formula (VIII) in the presence of a base and a catalyst.
Figure BDA0001815266310000112
In the formula, X, R1、R2、R3、R8、R9T and n are as described above.
Examples of the base used in the present reaction include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate, and potassium phosphate. The amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (VI).
Examples of the catalyst used in the present reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, and [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium. The amount of the catalyst to be used is usually 0.001 to 0.5 molar equivalent, preferably 0.01 to 0.2 molar equivalent, relative to the compound of the formula (VI). Further, as the catalyst, a phase transfer catalyst may be used. Examples of the phase transfer catalyst used in the present reaction include quaternary alkylammonium salts such as tetrabutylammonium bromide and tetrabutylammonium chloride. The amount of the phase transfer catalyst to be used is usually 0.001 to 1.0 molar equivalent, preferably 0.01 to 0.7 molar equivalent, relative to the compound of the formula (VI).
The reaction is generally carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inactive to the reaction, and for example, aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol, propanol, etc.; diethyl ether, di
Figure BDA0001815266310000121
Ethers such as alkane, THF, dimethoxyethane and the like; ketones such as acetone and methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or a mixed solvent thereof.
In this reaction, a ligand may be added as required. Examples of the ligand include 2-dicyclohexylphosphinyl-2 ', 6' -dimethoxybiphenyl and the like. The amount of the ligand to be used is usually 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, to the compound of the formula (VI).
The amount of the compound of formula (VII) or the compound of formula (VIII) used in the present reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of formula (VI).
The reaction temperature of the reaction is usually 0 to 180 ℃, preferably 30 to 150 ℃. The reaction time of this reaction is usually 10 minutes to 100 hours.
After the completion of the reaction, the compound of formula (V) can be isolated by, for example, mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the obtained organic layer, and purifying by silica gel column chromatography.
The compound of the formula (VII) is a known compound, or can be produced from a known compound by a known method.
The compound of formula (VI) is a known compound, or can be produced from a known compound by a known method. For example, the compound of formula (VI) can be produced by the method described in, or a method based on, ジャーナル, オブ, ヘテロサイクリック, ケミストリー (J.heterocyclic. chem.), volume 33, pages 1579 to 1582 (1996).
[ production method 6]
The compound of formula (VIII) can be produced by reacting a compound of formula (IX) with a compound of formula (X) in the presence of a base and a catalyst.
Figure BDA0001815266310000131
In the formula, X, R3、R9And n is as described above.
Examples of the base used in the present reaction include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate, potassium phosphate, and potassium acetate. The amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (IX).
Examples of the catalyst used in the present reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, and tris (dibenzylideneacetone) dipalladium. The amount of the catalyst to be used is usually 0.001 to 0.5 molar equivalent, preferably 0.01 to 0.2 molar equivalent, relative to the compound of the formula (IX).
The reaction is generally carried out in the presence of a solvent. As a solvent for the solvent, a solvent,the reaction is not particularly limited as long as it is inactive, and aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol, propanol, etc.; diethyl ether, di
Figure BDA0001815266310000132
Ethers such as alkane, THF, dimethoxyethane and the like; ketones such as acetone and methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or a mixed solvent thereof.
In this reaction, a ligand may be added as required. Examples of the ligand include tricyclohexylphosphine, 2-dicyclohexylphosphino-2 ', 6' -dimethoxybiphenyl, and the like. The amount of the ligand to be used is usually 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, to the compound of the formula (IX).
The amount of the compound of formula (X) used in the present reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of formula (IX).
The reaction temperature of the reaction is usually 0 to 180 ℃, preferably 30 to 150 ℃. The reaction time of this reaction is usually 10 minutes to 100 hours.
In addition, the reaction may be carried out by microwave irradiation, and in this case, the reaction may be accelerated.
After the completion of the reaction, the compound of formula (VIII) can be isolated by, for example, mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the obtained organic layer, and purifying by silica gel column chromatography.
[ production method 7]
The compound of the formula (IX) can be produced by reacting a compound represented by the formula (XI) with a compound represented by the formula (XII) in the presence of a base and a catalyst.
Figure BDA0001815266310000141
In the formula, X, R3、R9And n is as described above.
Examples of the base used in the present reaction include inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, cesium carbonate and potassium phosphate; organic bases such as triethylamine and diisopropylethylamine. The amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (XI).
Examples of the catalyst used in the present reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, and tris (dibenzylideneacetone) dipalladium. The amount of the catalyst to be used is usually 0.001 to 0.5 molar equivalent, preferably 0.01 to 0.2 molar equivalent, relative to the compound of the formula (XI).
The reaction is generally carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inactive to the reaction, and aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol, propanol, etc.; diethyl ether, di
Figure BDA0001815266310000142
Ethers such as alkane, THF, dimethoxyethane and the like; ketones such as acetone and methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or a mixed solvent thereof.
In this reaction, a ligand may be added as required. Examples of the ligand include tricyclohexylphosphine, 2-dicyclohexylphosphino-2 ', 6' -dimethoxybiphenyl, 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene, and the like. The ligand is used in an amount of usually 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound of formula (XI).
The amount of the compound of the formula (XII) used in the present reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of the formula (XI).
The reaction temperature of the reaction is usually 0 to 180 ℃, preferably 30 to 150 ℃. The reaction time of this reaction is usually 10 minutes to 100 hours.
After the completion of the reaction, the compound of formula (IX) can be isolated by, for example, mixing the reaction mixture with water, extracting with an organic solvent, drying and concentrating the obtained organic layer, and purifying by silica gel column chromatography.
The compound of the formula (XI) may be a known compound, or may be produced from a known compound by a known method.
The compound of the formula (XII) is a known compound.
[ production method 8]
The compound of the formula (IX) can be produced by reacting a compound represented by the formula (XIII) with a compound represented by the formula (XIV) in the presence of a base.
Figure BDA0001815266310000151
In the formula, X, R3、R9T and n are as described above.
Examples of the base used in the present reaction include metal alkoxides such as potassium tert-butoxide; inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride. The amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (XIII).
The reaction is generally carried out in the presence of a solvent. The solvent is not particularly limited as long as it is inactive to the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; diethyl ether, di
Figure BDA0001815266310000152
Ethers such as alkane, THF, dimethoxyethane and the like; amides such as DMF; sulfoxides such as DMSO; nitriles such as acetonitrile; ketones such as acetone; or a mixed solvent thereof.
The amount of the compound of formula (XIV) used in the present reaction is usually 0.5 to 3 molar equivalents, preferably 1 to 2 molar equivalents, relative to the compound of formula (XIII).
The reaction temperature of the reaction is usually 0 to 200 ℃, preferably 20 to 100 ℃. The reaction time of this reaction is usually 10 minutes to 30 hours.
After the completion of the reaction, for example, the compound of formula (IX) can be isolated by adding an acid to the reaction mixture to neutralize it, mixing it with water, extracting it with an organic solvent, drying and concentrating the obtained organic layer, and purifying it by silica gel column chromatography.
The compound of formula (XIII) is a known compound, or can be produced from a known compound by a known method.
The production method of the intermediate used for producing the compound of the present invention is not limited to the above-exemplified production method, and any production method can be employed. Further, each starting material is not limited to the above exemplified compounds, and any optional compound may be used as long as it can produce the compound of the present invention.
The compounds of the present invention can control a wide range of undesirable plants such as annual and perennial weeds. Specifically, for example, barnyardgrass (barnyardgrass: (barnyardgrass)Echinochloa crus-galli L.、Echinochloa oryzicolavariation), raised crabgrass (crabgrass: (crabgrass))Digitaria sanguinalis L.、Digitariaischaemum Muhl.、Digitaria adscendens Henr.、 Digitaria microbachneHenr.、Digitaria horizontalisWilld.), green foxtail (green foxtail: (green)Setaria viridisL.), herba Setariae viridis (giant foxtail: (L.))Setaria faberiHerrm.), green bristlegrass (yellow foxtail: (R))Setaria lutescensHubb.)), goosegrass (goose grass: (goose grass))Eleusine indicaL., L.), herba Avenae Fatuae (wild oat: (wild oat) ((wild oat))Avena fatuaL.), Erythrochloe (johnsongsas: (L.))Sorghum halepenseL.), Elytrigia repens (quarkgrass: (L.))Agropyron repensL.), brachypodium clavatum (alexandergrass: (Alexandrigrass))Brachiaria plantaginea) Sorghum saccharatum (guineagrass)Panicum maximumJacq.), Panicum virginiana (paragaras: (jagaras))Panicum purpurascens) Sorghum millet (smooth with grapevine) ()Panicum dichotomiflorum) Semen Euphorbiae (sporangetop: (sporangetop)Leptochloa chinensis) (iii) nits and fruit (red spangletop: (R) (R))Leptochloa panicea) Annual bluegrass (annual bluegrass)Poa annuaL.), and black grass (black grass: (L.))Alopecurus myosuroides Huds.、Alopecurus aequalisSobol.), Aminogras (chorodado blue (R) ((R))Agropyrontsukushiense(Honda) Ohwi)), Brachypodium arborescens (Broadleaf signakgrass ((Honda)) and (Hawsi) ((Honda) Ohwi))Brachiaria platyphyllaNash), puncturevine caltrop herb (southern sandbur: (Nash))Cenchrus echinatusL.), Lolium multiflorum (italian ryegrass: (L.))Lolium multiflorumLam.), ryegrass (rigid ryegrass: (Lam.))Lolium rigidumGaud.), sparassis (peak grass (r) ((r))Bromus tectorumL.), Bermudass (Bermudass: (L.))Cynodon dactylonPers.)))); cyperus rotundus (rice flatsedge: (A))Cyperus iriaL.), rhizoma Cyperi (purple nutsiedge: (Chinese character of 'xiangfu')Cyperus rotundusL.), Cyperus esculentus (yellow nutsodge.) (Cyperus esculentusL.), Fluoroxylum (Japanese bulrush) (see (R))Scirpus juncoides) Cyperus rotundus (flatsedge: (a)Cyperus serotinus) Cyperus rotundus (small-flower umbellipalant: (a))Cyperus difformis) Cow felt (slinder spikerush: (L.), (B.))Eleocharis acicularis) Water chestnut (water chestnut) (II)Eleocharis kuroguwai) Sedge weeds (cyperaceae); arrowhead (Japanese ribbon waparo) (Sagittaria pygmaea) Arroww-head (Arroww-head)Sagittaria trifolia) Alismatis rhizoma (narrowleaf Waterplantain: (a)Alisma canaliculatum) Alismatis weeds (alimataceae); herba Monochoria (Monochoria)Monochoria vaginalis) (ii), Podospora cordata (monochoria species), (b), (c), (d) and d), (d) and d), (d) and d) b) and d), (d) and d), (d) and d)Monochoria korsakowii) A sedentaceae weed (pontederiaceae); vegetables of strange origin (false pimpernel: (Lindernia pyxidaria) Weeds of the family of mother grass and Tabanus eyes (abuneme: (a))Dopatrium junceum) Plantaginaceae weeds (plantaginaceae); herba Oenotherae Erythrosepalae (root of Equisetum Arvinsis (Toothcup)Rotalaindia) Amaranthus mangostanus (red stem) (A. nannieri)Ammannia multiflora) A lythraceae weed (lythraceae); herba Stellariae mediae (long stem Waterwort), (A), (B), (C), (Elatine triandraSCHK.)) of the family hamamelidaceae (elasnaceae); piemarker (velvetleak: (velvetleak)Abutilon theophrastiMEDIC), and Sida acuta (privcly sida) (I.D.)SidaspinosaL.)) of the malvaceae family (malvaceae); xanthium sibiricum (common cocklebur: (Xanthium strumariumL.), (common ragweed: (A))AmbrosiaelatiorL.), thistle (thistle: (A)Breea setosa(BIEB.) KITAM.), Taurus majus (hair galinsoga: (BIEB.))Galinsoga ciliataBlake), chamomile (wild chamomile: (wild chamomile))Matricaria chamomillaL.), herba Lamii Amplexicaulis (henbit), (henbit)Lamium amplexicauleL.), herba Taraxaci (common Dandelion: (B.))Taraxacumofficinaleweber), erigeron canadensis (horseweed), (f)Erigeron CanadensisL.)) such as a compositae weed (compositae); black night shade (black night shade)Solanum nigrumL.), Datura (jimsonweed: (jimsonweed) ((L.))Datura stramonium) Solanaceae weeds (solanaceae); amaranthus rugosus (slinder amaranth: (A)Amaranthus viridisL.), Amaranthus retroflexus (redroot pigweed: (Amaranthus retroflexus)Amaranthus retroflexusL.), Chenopodium album (common lambsquarers), (L.), (Chenopodium albumL.), Kochia scoparia (mexican burning bush) (Kochia scopariaSchrad.)) of amaranth family (amaranthaceae); polygonum flaccidum (small smartweed), (A. tamarind)Polygonum lapathifoliumL.), herba Polygoni Hydropiperis (ladysthumb), (Ladyshumb)Polygonum persicariaL.), herba Polygoni Hydropiperis (wild buckwhaat: (wild)PolygonumconvolvulusL.), herba Polygoni Avicularis (knotted: (herba Polygoni Avicularis)Polygonum aviculareL.)) of the polygonaceae family (polygonaceeae); cardamine flexuousi (flexuous bittercress), (b)Cardamine flexuosaWITH.), shepherd's-core (Capsella bursapastorisMedik.), mustard (Indian mustard: (mustard)Brassica junceaCzern.)) of the brassicaceae family (cruciferae); morning glory (tall morninggrory)Ipomoea purpureaL.), Convolvulus arvensis (field bounded weed: (A))Convolvulus arvensisL.)), morning glory (ivyleaf horningglory: (ivyleaf horningglory))Ipomoea hederaceaJacq.)) of the family Convolvulaceae (convoluulaceae); purslane (common pursan: (A))Portulaca oleraceaL.)) of the Portulacaceae family (Portulacaceae); cassia obtusifolia (sicklepod: ()Cassia obtusifoliaL.)) of legume weeds (fabaceae); chickweed (common chickweed: (StellariamediaL.)) of the family caryophyllaceae; saw stem (cathweded)(Galium spuriumL.)) of the rubiaceae family (rubiaceae); acalypha australis (threeeeded copperleaf: (A)Acalypha australisL.)) of the euphorbiaceae family (eupolyphbiaceae); commelina communis (common dayflower: (Commelina communisL.)) of the Commelinaceae family (Commelinaceae). Thus, the compounds of the invention are useful in crops of useful plants, such as maize (corn: (a)Zea maysL.), soybean (soybean: (L.))Glycine maxMerr.), cotton (cotton:)Gossypiumspp.), wheat (wheat: (wheat))Triticum aestivumL.), rice (rice: (rice) (rice)Oryza sativaL.), barley (barley: (barley) (barley)Hordeum VulgareL.), rye (rye: (L.))SecalecerealeL.), oat (oat: (a))Avena sativaL.), sorghum (sorgo:)Sorghum bicolorMoench), rape (rape:)Brassica napusL.), sunflower (sunflower: (sun flower) ((g.))Helianthus annuusL.), sugar beet (sugar beet: (Beta VulgarisL.), sugarcane (sugar cane: (L.))Saccharum officinarumL.), zoysia (Japanese lawn) (L.), (Zoysia japonica stend) Peanut (peanout: (b))Arachis hypogaea L.), flax (f) (a)LinumusitatissimumL.), tobacco (tobaco: (L.))Nicotiana tabacumL.), coffee (coffee: (coffee)Coffeaspp.)) and the like, are effectively used in the case of selectively controlling harmful weeds or in the case of non-selectively controlling harmful weeds.
The compound of the present invention can be used in various forms such as powder, granule, water-dispersible granule, wettable powder, tablet, pill, capsule (including a form packaged with a water-soluble film), aqueous suspension, oil suspension, microemulsion, suspoemulsion, soluble powder, emulsion, soluble liquid preparation, paste, etc., by mixing with various agricultural adjuvants.
Examples of adjuvants used in the preparation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, and kaolinSolid carriers such as lingshi, sericite, clay, sodium carbonate, sodium bicarbonate, Natrii sulfas, zeolite, and starch; water, toluene, xylene, solvent naphtha, di
Figure BDA0001815266310000191
Solvents such as alkanes, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and alcohols; fatty acid salts, benzoic acid salts, alkylsulfosuccinic acid salts, dialkylsulfosuccinic acid salts, polycarboxylic acid salts, alkyl sulfate salts, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, alcohol sulfate salts, alkylsulfonic acid salts, alkylaryl sulfonic acid salts, arylsulfonic acid salts, lignosulfonic acid salts, anionic surfactants or spreaders such as alkyldiphenyl ether disulfonates, polystyrene sulfonates, alkyl phosphate ester salts, alkylaryl phosphates, styrylaryl phosphates, polyoxyethylene alkyl ether sulfate ester salts, polyoxyethylene alkylaryl ether sulfate ester salts, polyoxyethylene alkyl ether phosphate salts, polyoxyethylene alkylaryl phosphate ester salts, polyoxyethylene aryl ether phosphate ester salts, naphthalene sulfonate formaldehyde condensates, and alkylnaphthalene sulfonate formaldehyde condensates; nonionic surfactants or spreaders such as sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid alcohol polyglycol ethers, acetylene glycols, acetylene alcohols, oxyalkylene block polymers, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylaryl ethers, polyoxyethylene glycol alkyl ethers, polyethylene glycols, polyoxyethylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oils, and polyoxypropylene fatty acid esters; or vegetable oil or mineral oil such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, liquid paraffin, etc. As long as the object of the present invention is not exceeded, 1 or 2 or more of these may be appropriately selected and usedThese adjuvants. In addition, various auxiliary agents generally used, such as an extender, a thickener, a sedimentation preventing agent, an antifreezing agent, a dispersion stabilizer, a safener, a fungicide, a foaming agent, a disintegrating agent, and a binder, can be used. The compounding ratio of the compound of the present invention to various adjuvants is usually 0.1: 99.9 to 95: 5, preferably 0.2: 99.8-85: 15. the method for mixing the compound of the present invention with various adjuvants is not particularly limited, and the compound can be appropriately mixed according to a known method.
The amount of the herbicide containing the compound of the present invention to be applied (herbicidally effective amount) cannot be generally specified depending on weather conditions, soil conditions, formulation forms, types of the target undesired plants, application time, and the like, but the amount of the compound of the present invention to be applied (hereinafter, also referred to as the effective component amount) per 1 hectare is preferably 0.1 to 5,000g, more preferably 0.5 to 3,000g, still more preferably 1 to 1,000g, and particularly preferably 10 to 500 g. The present invention also includes a method for controlling undesired plants by applying such a herbicide.
In addition, the herbicide containing the compound of the present invention may be used alone, or may be used in combination with or mixed with other agricultural chemicals, fertilizers, safeners, and the like. When used in combination or mixed, the composition may exhibit more excellent effects and effects. Examples of the other agricultural chemicals include herbicides, bactericides, antibiotics, plant hormones, and insecticides. In particular, a mixed herbicidal composition obtained by mixing or using 1 or 2 or more kinds of the compounds of the present invention and other herbicides as active ingredients can improve the range of applicable grass seeds, the timing of drug treatment, herbicidal activity, and the like in a desirable direction. The compound of the present invention and a compound as an active ingredient of another herbicide may be separately formulated and used in admixture for spreading, or both may be formulated and used together. The present invention also includes the above mixed herbicidal composition.
The mixing ratio of the compound of the present invention and the compound as the active ingredient of the other herbicide cannot be generally defined depending on weather conditions, soil conditions, pharmaceutical preparation form, application time, application method and the like, but the other herbicide is preferably added in an amount of 0.001 to 10,000 parts by weight, more preferably 0.01 to 1,000 parts by weight, per 1 part by weight of the compound of the present invention. In addition, the amount of the active ingredient is preferably 0.1 to 10,000g, more preferably 0.2 to 5,000g, and still more preferably 10 to 3,000g, per 1 hectare. The present invention also includes a method for controlling undesired plants by applying such a mixed herbicidal composition.
Examples of the compounds as the active ingredient of other herbicides include the following compounds (1) to (12) (common names; including some ISO applications), and if not specifically described, salts, alkyl esters, and the like are present in these compounds, they are naturally also included.
(1)2,4-D, 2,4-D butoxyethyl ester (2,4-D-butyl), 2,4-D butyl ester (2,4-D-butyl), 2,4-D dimethylammonium (2, 4-D-dimethyllamonimum), 2,4-D dialkanolamine (2,4-D-diolamine), 2,4-D ethyl ester (2,4-D-ethyl), 2,4-D-2-ethylhexyl ester (2,4-D-2-ethylhexyl), 2,4-D isobutyl ester (2,4-D-isobutyl), 2,4-D isooctyl ester (2,4-D-isoctyl), 2,4-D isopropyl ester (2,4-D-isopropyl), 2,4-D isopropylammonium (2, 4-D-isopropyllammonium), 2,4-D sodium (2,4-D-sodium), 2,4-D-isopropylammonium (2, 4-D-isopropyllammonium), 2,4-D triethanolamine (2, 4-D-tromamine), 2,4-DB butyl ester (2,4-DB-butyl), 2,4-DB dimethylammonium (2, 4-DB-dimethyllammonium), 2,4-DB isooctyl ester (2,4-DB-isoctyl), 2,4-DB potassium (2,4-DB-potassium), 2,4-DB sodium (2,4-DB-sodium), 2,4-D choline (2, 4-D-cholelsalt), 2,4-D propionic acid (diorprop), 2,4-D butoxyethyl propionate (2, 4-chlorothiobutyl), 2,4-D-butyl propionate (2, 4-D-chloro-butyl), 2, 4-D-D-butyl propionate (2, 4-D-chloro-butyl), etc, Dimethyl ammonium 2, 4-dipropionate (dichlorprop-dimthyllamonium), isooctyl 2, 4-dipropionate (dichlorprop-isoctyl), potassium 2, 4-dipropionate (dichlorprop-potassium), high-2, 4-dipropionate (dichlorprop-P), dimethyl ammonium high-2, 4-dipropionate (dichlorprop-P-dimyrium), potassium 2, 4-dipropionate (dichlorprop-P-potassium), sodium 2, 4-dipropionate (dichlorprop-P-potassium), MCPA-butoxyethyl ester (MCPA-butotyyl), MCPA dimethyl ammonium (MCPA-dimyrium), MCPA-2-ethylhexyl (MCPB-2-ethylhexpb), potassium MCPA (MCPA-potassium), sodium MCPA-sodium (MCPA-sodium), MCPA-2-ethylhexylPB), MCPA (MCPA-sodium), MCPA-sodium (MCPA-sodium), MCPA-dimethylsulfoacetate (MCPA-sodium), MCPA-sodium MCPA (MCPA-sodium MCPA-dipotassium), MCPA-2-propylPB (MCPB), MCPA (MCPA-2-sodium MCPA, MCPB), MCPA-sodium MCPA (MCPA-sodium MCPA-2-sodium MCPA, MCPB), MCPB, MCPA-sodium MCPA-2-sodium MCPA-4-2-sodium MCPA-2-sodium MCPA-P-sodium MCPA-2-sodium MCPA, MCPB, MCPA-MCPB, MCPA-MCPB, MCPA-4, MCPA-MCPA, MCPA, Phenoxy compounds such as 2-4-chloropropionic acid (mecoprop), 2-4-butoxyethyl chloropropionate (mecoprop-butoxyl), sodium 2-4-chloropropionate (mecoprop-sodium), high-2-4-chloropropionic acid (mecoprop-P), high-2-4-butoxyethyl chloropropionate (mecoprop-P-butoxyl), high-2-4-dimethylammonium chloropropionate (mecoprop-P-dimethylammonium), high-2-4-chloropropionic acid 2-ethylhexyl (mecoprop-P-2-ethylhexyl), high-2-4-potassium chloropropionate (mecoprop-P-potassium), naphthylamine (naproxide), chloroformamidine (mecoprop), and HIA-1; 2,3,6-TBA, dicamba (dicamba), dicamba butoxyethyl ester (dicamba-butyl), dicamba diglycolamine (dicamba-diglycolamine), dicamba dimethylammonium (dicamba-dimethyllammonium), dicamba diglycolamine (dicamba-diolamine), dicamba isopropylammonium (dicamba-isopyrammonia), dicamba potassium (dicamba-potassium), sodium dicamba (dicamba-sodium), picloram (picloram), picloram dimethyl ammonium picloram (picloram-dimonium), picloram isooctyl piclorate (picloram-isocynamide), potassium picloram (picloram-potatatum), picloram triisopropanolamine (picloram-isopropyl), picloram-isopropyl alcohol (picloram-isopropyl alcohol), picloram potassium picloram (picloram-isopropyl alcohol), picloram-isopropyl alcohol (isopropyl alcohol), picloram-isopropyl alcohol (isopropyl alcohol, ethyl ester (picloram-isopropyl alcohol, picloram-isopropyl alcohol (isopropyl alcohol, picloram, isopropyl alcohol (isopropyl alcohol, isopropyl, Aromatic carboxylic acid compounds such as triclopyr triethylammonium (triclopyr-triethylammonium), clopyralid (clopyralid), clopyralid-olamine (clopyralid-amine), potassium clopyralid (clopyralid-potassium), clopyralid-triisopropanolammonium (clopyralid), aminopyralid (aminopyralid), aminocyclopyralid (aminocyclopyralid), halauxifen-methyl, and DAS-534; or naproxen (naptalam), naproxen sodium (naptalam-sodium), benazolin (benazolin), benazolin ethyl ester (benazolin-ethyl), quinclorac (quinclorac), chloroquinac (quinmerac), diflufenzopyr (diflufenzopyr), fluroxypyr-sodium (diflufenzopyr-sodium), fluroxypyr (fluroxypyr), fluroxypyr-2-butoxy-1-methylethyl (fluroxypyr-2-butoxy-1-methythioyl), fluroxypyr-isooctyl (fluroxypyr-meptyl), trufflnol (chloroflufluroxyphenol), trufflholmethyl ester (chloroflufluroxyphenol-methyl), clofenprophos (clophyfos) and the like, which show efficacy by disrupting the action of hormones of plants.
(2) Urea compounds such as chlortoluron (chlorotoluron), diuron (diuron), fluometuron (fluometuron), linuron (linuron), isoproturon (isoproturon), pyrone (metobenzuron), buthiuron (tebuthiuron), oxazolon (dimefuron), isoproturon (isouron), triamcinolone (karbutilate), methabenzthiazuron (methabenzthioron), metoxuron (metoxuron), bromuron (metoxuron), monoluron (monolinuron), neburon (neburon), cyclouron (siduron), terbuton (terbumeton), and metribuzin (trietazine); triazine compounds such as simazine, atrazine, simetone, simetryn, prometryn, isopentane, hexazinone, metribuzin, terbuthylazine, cyanazine, ametryn, cybutryne, terbutryn, prometryn, metamitron, prometryn, metribuzin, prometryn, prometron, and prometron; uracil compounds such as bromacil (bromacil), bromacil-lithium (bromacil-lithium), lenacil (lenacil) and terfenal (terbacil); anilide compounds such as propanil (propanil) and cyprodinil (cyproamid); carbamate compounds such as swep, desmedipham, and phenmedipham; hydroxybenzonitrile-based compounds such as bromoxynil (bromoxynil), bromoxynil octanoate (bromoxynil-octanoate), bromoxynil heptanoate (bromoxynil-heptanoate), iodoxynil (ioxynil-octanoate), potassium iodoxynil-potassium, and sodium iodoxynil-sodium; and compounds that exhibit herbicidal effects by inhibiting photosynthesis of plants, such as pyridate (pyridate), bentazone (bentazone), bentazone sodium (bentazone-sodium), amicarbazone (amicarbazone), mefenpyr (methazole), mechlorfenchloramide (pentaochlor), and phenmedipham.
(3) Quaternary ammonium salt compounds such as paraquat and diquat which themselves are free radicals in plants and generate active oxygen to exhibit a quick-acting herbicidal effect.
(4) Diphenyl ether compounds such as bifenox (nitrofen), acifluorfen (chlorothoxyfen), bifenox (bifenox), acifluorfen (acifluorfen), acifluorfen-sodium (acifluorfen-sodium), fomesafen (fomesafen), fomesafen-sodium (fomesafen-sodium), oxyfluorfen (oxyfluorfen), lactofluorfen (lactofen), aclonifen (aclonifen), fluroxypyr, fluoroglycofen-ethyl (ethoxyfluoroglycofen-ethyl), fluoronitrofen (fluoroglycofluorfen); cyclic imide compounds such as chlorophthalimide (chlorophhthalim), propyzamide (flumioxazin), fluoroeleaf (fluriclorac), flumiclorac-pentyl (flumiclorac-pentyl), cinidon-ethyl (cinidon-ethyl), fluthiacet-methyl (fluthiacet-methyl), and EK-5385; or oxadiargyl (oxadiargyl), oxadiazon (oxadiargyl), sulfentrazone (sulfentrazone), carfentrazone-ethyl, thidiazuron (thiazimin), pentoxazone (pentoxazone), azafenidin (azafenidin), flubromate (isoproxazole), pyriproxyfen (pyraflufen-ethyl), benezolidone (benzofenamidone), butafenacil (butafenacil), saflufenacil (saflufenacil), isobutafenacil (fluazonate), flumetsulam (profluazol), flupyridazinyl (flunpyrazole), bencambarazone, tiferacil, difenoconazole (pyrachlonil), trifluoxazine (fluazin-ethyl), flumethazine (flufenamidopropyl), flumetz (flufenamidopropyl-ethyl), fenpyr (flufenamidopropyl), benzofenazazole, tiferacil (pyraclonil), trifluozin (trifluo 40404040404096), thiodazon-5447, thiofenamidone (fenpyr-ethyl), thiodazole (FM63523, PC-008763, PC-like compounds described in plants, such as phytolachlorfenflurazone, flumicloracil-3548, Acineton (FMolinil, flumicloracil, Spiro, Sporozin, Spiro-008763, Spiro-3548, Spiro, PC-3548, Spiro, Spirofon, PC-3548, E-E, PC-E, E-54523, a compound which exhibits herbicidal efficacy by abnormally accumulating a photosensitized peroxygen substance in a plant body.
(5) Pyridazinone compounds such as norflurazon (norflurazon), chlorpyrifos (chloridazon) and metaflurazon (metaflurazon); pyrazolate (pyrazolynate), pyraclonil (pyrazoxyfen), benzofenap (benzofenap), and pyrazopyrPyrazole compounds such as ketone (topramezone), pyrasulfotole (pyrasulfotole) and tolpyralate; or imazapyr (amisole), fluridone (fluridone), flurtamone (flurtamone), diflufenican (diflufenican), benzotolone (methamphenone), clomazone (clomazone), sulcotrione (sulcotrione), mesotrione (mesotrione), tembotrione (tembotrione), tefurylketone (tefuryltrione), fenquilrione, cycloprozole, isoxathimide, flutolanil (isoxapyroxate), flutolone (flutolanil), flutolanil (flutolanil), fluquinotrine (cyclomycin (isoxate), flutolanil (isoxate), flutole), fluquinacr (isoxate(s), fluquinacridone (fluquinone), fluquinacr(s), fluquinone, flubenfluranil(s), fluquinacr(s), flubenfluranil) and/or a(s) and/or a (isoxapyroxapyroxate(s) or a (s, or a(s) or (s, or(s) or (s, or(s) or (s, or(s) or (s, or(s) or
Figure BDA0001815266310000241
Carfentrazone-ethyl (isoxaflutole), difenzoquat (difenzoquat), difenzoquat-methosulfate, isoxaflutole
Figure BDA0001815266310000242
Examples of the compound include compounds which inhibit the biosynthesis of pigments in plants such as carotenoids and exhibit a herbicidal effect characterized by a whitening effect, such as clomazone (isoxachlorotolole), benzobicyclon (benzobicyclon), bicyclopyrone (bicyclopropyrone), picolinafen (picolinafen), beflubutamid (beflubutamid), ketospiradox-potassium, and the compounds described in JP 2012-2571 (sumitomo chemical).
(6) Diclofop-methyl, pyriphenop-sodium, fluazifop-butyl, haloxyfop-methyl, haloxyfop-ethyl, haloxyfop-P-methyl, haloxyfop-P-ethyl, quizalofop-ethyl, haloxyfop-P-methyl, haloxyfop-ethyl, haloxyfop-methyl, haloxyfop-ethyl, haloxyfop-methyl, haloxyfop-ethyl, haloxyfop-methyl, halofop-methyl, haloxyp-methyl, haloxyfop-methyl, halofop-ethyl, halofop-methyl, halofop-ethyl, halofop-ethyl, halofop-methyl, halofop-ethyl, halofop-methyl, halofop-methyl, halofop-ethyl, halofop-methyl, halofop-ethyl, halofop-methyl, halofop, halo, Aryloxyphenoxypropionic acid compounds such as fenoxaprop-P (fenoxaprop-P), fenoxaprop-P-ethyl (fenoxaprop-P-ethyl), metamifop-propyl (memifop), metamifop (metamifop), clodinafop-propargyl (clodinafop), clodinafop (clodinafop), oxaprozin (propaquizafop), HNPC-a8169, and SYP-1924; cyclohexanedione compounds such as sodium gramininate (alloxydim-sodium), dicumyl (alloxydim), clethodim (clethodim), sethoxydim (sethoxydim), tralkoxydim (tralkoxydim), butroxydim, tepraloxydim, cyclobenzophenone (profoxdim), cycloxydim (cycloxydim); phenylpyrazoline compounds such as pinoxaden; and compounds which inhibit the biosynthesis of fatty acids and exhibit herbicidal effects on plants.
(7) Chlorimuron-ethyl (chlorimuron-ethyl), sulfometuron-methyl (sulfometuron), primisulfuron-methyl (primisulfuron-methyl), bensulfuron-methyl (bensulfuron), chlorsulfuron (chlorimuron-methyl), methylsulfuron-methyl (methylsulfuron-methyl), sulfometuron (sulfamuron-methyl), sulfometuron (methylsulfuron), sulfosulfuron (cinosulfuron), pyrosulfuron-methyl (pyrosulfuron-ethyl), pyrosulfuron-ethyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron), pyrosulfuron-methyl (sulfosulfuron), pyrosulfuron (pyrosulfuron), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron (pyrosulfuron), pyrosulfuron-methyl (pyrosulfuron), pyrosulfuron-methyl), pyrosulfuron (pyrosulfuron), pyrosulfuron-methyl), pyrosulfuron (pyrosulfuron), pyrosulfuron-methyl), pyrosulfuron (pyrosulfuron-methyl (pyrosulfuron), pyrosulfuron-methyl), pyrosulfuron (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl), pyrosulfuron-methyl (pyrosulfuron-methyl, pyrosulfuron-methyl, pyrosulfuron-methyl, pyrosulfuryl-methyl, pyrosulfuron-methyl, pyro, Triflusulfuron-methyl (triflusulfuron), halosulfuron-methyl (halosulfuron-methyl), halosulfuron-methyl (halosulfuron), thifensulfuron-methyl (thifensulfuron-methyl), ethoxysulfuron (ethosulfuron), epoxysulfuron (oxasulfuron), fensulfuron-methyl (ethosulfuron-methyl), iodosulfuron-methyl (iodosulfuron), iodosulfuron-sodium (iodosulfuron-methyl-sodium), sulforon (sulfosulfuron), sulforon (sulforon), sulforon (triasulfuron), tribenuron-methyl (triflussulfuron), sulfosulfuron (triflusulfuron-methyl), sulfamuron (sulfamuron-methyl), sulfamuron-methyl (triflusulfuron-methyl), sulfamuron-methyl (sulfamuron-methyl), sulfamuron-methyl (sulfamuron-methyl), sulfamuron (triflusulfuron-methyl), sulfamuron (sulfamuron-methyl), sulfamuron (sulfamuron-methyl), sulfamylon-methyl (sulfamylon-methyl), sulfamylon-methyl (sulfamylon-methyl), sulfamylon-methyl (sulfamylon-methyl, sulfamylon-methyl (sulfamylon-methyl, sulfamylon (sulfamylon-methyl, sulfamylon (sulfamylon-methyl, sulfamylon (sulfamylon-methyl, sulfamylon (sulfamylon-methyl, sulfamylon-methyl, sulfamylon (sulfamylon-methyl, sulfamylon, Sulfonylurea compounds such as amidosulfuron (amidosulfuron), azimsulfuron (azimsulfuron), propylrisulfuron, diethofenchloropyrazosulfuron (metazosulfuron), methiosulfuron (methiopyrsulfuron), monosulfuron-methyl, orsosulfuron, iofensulfuron, and iofensulfuron; triazolopyrimidine sulfonamide-based compounds such as flumetsulam (flumetsulam), metosulam (metosulam), diclosulam (diclosulam), cloransulam-methyl, florasulam (florasulam), penoxsulam (penoxsulam), and pyroxsulam (pyroxsulam); imidazolinone-series compounds such as imazapyr (imazapyr), imazapyr-isopropylammonium (imazapyr-isopyrammonium), imazethapyr (imazapyrapyr), imazethapyr-ammonium (imazapyr-ammonium), imazaquin (imazaquin), imazaquin-ammonium (imazaquin-ammonium), imazethapyr (imazamox), imazamox (imazamox-ammonium), imazamethabenz (imazamethabenz), imazamethabenz methyl ester (imazamethabenz-methyl), imazethapyr methyl ester (imazazapic); pyrimidinylsalicylic acid-based compounds such as pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim-methyl, pyrithiofan-methyl, and triafamone; sulfonamidocarbonyltriazolinone compounds such as flucarbazone, sodium flucarbazone-sodium, propylbensulfuron-methyl and thiencarbazone-methyl; or glyphosate (glyphosate), sodium glyphosate (glyphosate-sodium), potassium glyphosate (glyphosate-potassium), ammonium glyphosate (glyphosate-ammonium), diammonium glyphosate (glyphosate-ammonium), isopropylammonium glyphosate (glyphosate-isopyraponium), phosphinothricine (glyphosate-trimetium), sodium glyphosate (glyphosate-sesquisium), glufosinate (glufosinate-ammonium), glufosinate-P (glufosinate-P-ammonium), glufosinate-P (glufosinate-P-sodium), bialaphos-P (glufosinate-P-sodium), bialaphos (bialaphos-sodium), suberin (bialaphos-sodium), and the like, which inhibit the synthesis of herbicidal amino acids by plants.
(8) Dinitraniline compounds such as trifluralin (trifluralin), oryzalin (oryzalin), oryzalin (nitralin), pendimethalin (pendimethalin), ethylbutenofluorin (ethalfluralin), ethylbufalin (benfluralin), prodiamine (prodiamine), butralin (butralin), and dinitramine (dinitramine); amide compounds such as bensulide (bensulide), naproxamide (naproxamide), naproxamide-M (naproxamide-M), propyzamide (propyzamide), and naproxen (propamide); organic phosphorus compounds such as amiprofos-methyl, butamifos, anilofos and piperaphos; phenyl carbamate compounds such as propham (propham), chlorpham (chlorpham), barban (barban), and diacyl urea (carbetamide); cumylamine-based compounds such as jimuron (daimuron), cumyluron (cumyluron), bromobutyric acid (bromobutyide), and metyldyron (methydyron); or compounds which exhibit herbicidal effects by inhibiting the mitosis of plant cells, such as asulam (asulam), asulam-sodium (asulam-sodium), dithiopyr (dithiopyr), thiazopyr (thiozopyr), methylphosphonate (chlorothal-dimethyl), chlorophthalic acid (chlorothal), diphenoyl oxamide (diphenylamid), flamprop-methyl ester (flamprop-M-methyl), flamprop-M-isopropyl (flamprop-M-isopropyl), and the like.
(9) Alachlor (alachlor), metazachlor (metazachlor), butachlor (butachlor), metolachlor (pretilachlor), metolachlor (metolachlor), S-metolachlor (S-metolachlor), methoxychlor (theylchloride), pethoxamid (pethoxamid), acetochlor (acetochlor), propachlor (propachlor), dimethenamid (dimethenamid), dimethenamid-P (dimethenamid-P), propisochlor (propachlor), chloramide such as dimethenamid (dimethachloride)A compound of (a); thiocarbamate-based compounds such as molinate, dimerate, pyributicarb, EPTC, buthylate, vernolate, pellitorin, cycloate, prosulfocarb, esprocarb, thiobencarb, diolate, triallate, and prosulfocarb; or ethoxybenclamide (etobenzanid), mefenacet (mefenacet), flufenacet (flufenacet), dichlorbenzuron (tridephane), cafenstrole (cafenstrole), fentrazamide (fentrazamide),
Figure BDA0001815266310000281
And compounds exhibiting weed-removing effects by inhibiting protein biosynthesis or lipid biosynthesis of plants, such as metribuzin (oxazilomefone), indanthrone (indoofan), benfuresate (benfuresate), pyroxasulfone (pyroxasulfone), fenoxasulfone, methiozolin, dalapon (dalapon), dalapon-sodium, TCA-sodium, trichloroacetic acid (trichloroacetic acid), and the like.
(10) Dichlobenil (dichlobenil), triaziflam (triaziflam), indaziflam, flumetsulam (flupoxam), isoflumetsulam
Figure BDA0001815266310000282
And compounds such as oxamide (isoxaben) which exhibit herbicidal efficacy by inhibiting cellulose biosynthesis in plants.
(11) MSMA, DSMA, CMA, endoxygrass (endoxygrass), endoxygrass dipotassium (endoxygrass-dipotassium), endoxygrass sodium (endoxygrass-sodium), endoxygrass mono (N, N-dimethylalkylammonium) (endoxygrass-mono (N, N-dimethylalkylammonium), ethofumesate (ethofumesate), sodium chlorate (sodium chlorate), pelargonic acid (pelargonic acid), nonanoic acid (nonanic acid), glufosinate (fosamisole), glufosinate-ammonium, ipfencarbazone, acrolein (aclonimine), ammonium sulfamate (ammonium sulfamate), borax (borax), chloroacetic acid (chloroacetic acid), sodium chloroacetate (chloroacetate), ammonium cyanamide (thiocyanatecholate), ammonium carbamate (arsanilate), dimethylammonium (dimethylammonium), dimethylammonium chloride (arsanilate), dimethylammonium chloride (arsine), dimethylammonium chloride (arsanilate), dimethylammonium chloride (arsine-dimethylammonium chloride (arsine), dimethylammonium chloride (arsine), benzalkonium chloride (arsine), and salts of sodium chlorate), ammonium chloride (methyl pyrrolidone), sodium chloride (methyl pyrrolidone), sodium chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and sodium chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride (methyl chloride) and methyl chloride, sodium chloride (methyl chloride, sodium chloride, DNOC, ferrous sulfate (FERROUS SULFATE), tetrafluoropropionic acid (FLUPROPANE), sodium tetrafluoropropionate (FLUOROPROPANE-SODIUM), fluorosulfonamide (MEFLUIDIDE), fluorosulfonamide di-alcohol amine (MEFLUIDIDE-DIOLAMINE), metam (METAM), ammonium metamate (METAM-AMMONIUM), potassium metamate (METAM-POTASSIUM), sodium metamate (METAM-SODIUM), methyl isothiocyanate (METHYL ISOTHIOCYCLICANATE), pentachlorophenol (PENTACHLOPHENOPHENOL), sodium pentachlorophenolate (SODIUM PENTACHLOROPHENOOXIDE), pentachlorophenol laurate (TACHLOROPHENOPHENOL LAURATE), quinophthalone (quinophthalone), sulfuric acid (SULFURACID), urea sulfate (UREALFATE), xanthatin (xanthatin), herbimycin (METAPIN), propyzamide (METAPIS-DIMETAPIS), alpha-isopropyl methacrylate (METAPIS-isopropyl methacrylate), penoxsulindamine (METAPIS, alpha-propyl Methacrylate (METAPIS), penoxsulosin), xanthatin (METAPIS, xanthins), xanthatin (METAPIS, xanthatin, KHG-23844, H-9201, SIOC-0163, SIOC-0171, SIOC-0172, SIOC-0285, SIOC-0426, SIOC-H-057, ZJ-0166, ZJ-1835, ZJ-0453, ZJ-0777, ZJ-0862, and WO2008/096398 (chemical クミアイ).
(12) Xanthomonas campestris (A. campestris)Xanthomonas campestris)、Epicoccosirus nematosorus、Epicoccosirus nematosperusHippocampus angustifolia: (Exserohilum monoseras) Spirosoma echinochloa (I) and (II) of ProbenariaDrechsrela monoceras) And compounds which exhibit herbicidal effects by parasitizing plants.
The above-mentioned compounds as active ingredients of other herbicides may be selected from 1 or 2 or more as appropriate. The active ingredients of other herbicides are not limited to the compounds exemplified above.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the examples. First, examples of synthesis of the compounds of the present invention are described.
Synthesis example 1
Synthesis of 4- (5- ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) thio) -2-methylphenyl) -5-methoxy-2, 6-dimethylpyridazin-3 (2H) -one (Compound Nos. 1 to 32 described later)
(1) Under a nitrogen atmosphere, 2-bromo-4-iodo-1-methylbenzene (1.0g), (4-methoxyphenyl) methanethiol (520mg), tris (dibenzylideneacetone) dipalladium (80mg), 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (100mg), and 1, 4-bis
Figure BDA0001815266310000291
Diisopropylethylamine (1.2mL) was added to the mixture of the alkane solution (10mL) and the mixture was reacted under reflux for 1 hour. The reaction mixture was cooled, water was added, and extracted 2 times with ethyl acetate (30 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (heptane: ethyl acetate: 20: 1, capacity ratio, the same as below) to obtain (3-bromo-4-methylphenyl) (4-methoxybenzyl) sulfane (1.07g, yield 98%) as a brown oil. The NMR spectrum data of this substance are as follows.
1H NMR(300MHz,CDCl3):δppm＝2.35(3H,s),3.79(3H,s),4.04(2H, s),6.83(2H,d,J＝8.7Hz),7.08-7.21(4H,m),7.48(1H,d,J＝0.6Hz)
(2) (3-bromo-4-methylphenyl) (4-methoxybenzyl) sulfane (1.07g), bis (pinacolato) diboron (1.26g), tris (dibenzylideneacetone) dipalladium (120mg), tricyclohexylphosphine (150 mg), potassium acetate (490mg) and 1, 4-bis (phenylmethyl) phosphine under a nitrogen atmosphere
Figure BDA0001815266310000301
A mixed solution of an alkane (15ml) was reacted at 120 ℃ for 7 hours. The reaction mixture was cooled, insoluble solid material was removed by celite (celite), and the solid material was washed with ethyl acetate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (heptane: ethyl acetate ═ 20: 1), whereby 2- (5- ((4-methoxybenzyl) thio) -2-methylphenyl) -4,4,5,5-Tetramethyl-1, 3, 2-dioxaborolan (1.07g, 87% yield). The NMR spectrum data of the purified product are as follows.
1H NMR(300MHz,CDCl3):δppm＝1.38(12H,s),2.48(3H,s),3.77(3H, s),4.03(2H,s),6.80(2H,d,J＝8.4Hz),7.04(1H,d,J＝8.1Hz), 7.17-7.27(3H,m),7.76(1H,dd,J＝1.5Hz,J＝6.6Hz)
(3) Reacting 2- (5- ((4-methoxybenzyl) thio) -2-methylphenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (381mg), 4-bromo-5-methoxy-2, 6-dimethylpyridazin-3 (2H) -one (200mg), tetrakis (triphenylphosphine) palladium (40mg), sodium carbonate (200mg), tetrabutylammonium bromide (144mg), 1, 4-bis (diphenyl-phosphine)
Figure BDA0001815266310000302
A mixed solution of an alkane (6mL) and water (4mL) was reacted at 120 ℃ for 45 minutes. The reaction mixture was cooled, to which was added water, and then extracted with ethyl acetate (20ml) 2 times. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography (heptanes: ethyl acetate ═ 1: 1) to give 5-methoxy-4- (5- ((4-methoxybenzyl) thio) -2-methylphenyl) -2, 6-dimethylpyridazin-3 (2H) -one (275mg, yield 81%) as a white solid. The NMR spectrum data of the purified product are as follows.
1H NMR(300MHz,CDCl3):δppm＝2.16(3H,s),2.27(3H,s),3.24(3H, s),3.68(3H,s),3.77(3H,s),4.03(2H,s),6.79(2H,d,J＝8.7Hz),7.15-7.26(5H, m)
(4) 5-methoxy-4- (5- ((4-methoxybenzyl) thio) -2-methylphenyl) -2, 6-dimethylpyridazin-3 (2H) -one (275mg) was dissolved in trifluoroacetic acid (2ml), and reacted at 60 ℃ for 3 hours. The reaction mixture was cooled, and the solvent was distilled off under reduced pressure to obtain 4- (5-mercapto-2-methylphenyl) -5-methoxy-2, 6-dimethylpyridazin-3 (2H) -one (190mg, yield 99%) as a brown solid.
(5) A mixed solution of 4- (5-mercapto-2-methylphenyl) -5-methoxy-2, 6-dimethylpyridazin-3 (2H) -one (190mg), 2, 3-dichloro-5- (trifluoromethyl) pyridine (223mg), cesium carbonate (336 mg) and dimethylformamide (5ml) obtained in the above-mentioned step (4) was reacted at 60 ℃ for 3 hours. The reaction mixture was cooled, and after water was added to the mixed solution, it was extracted with ethyl acetate (20ml) 2 times. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (heptane: ethyl acetate ═ 3: 2), whereby the objective substance was obtained as a white solid (122mg, yield 39%). The NMR spectrum data of the purified product are as follows.
1H NMR(300MHz,CDCl3):δppm＝2.24(3H,s),2.30(3H,s),3.53(3H, s),3.73(3H,s),7.36-7.38(2H,m),7.48(1H,dd,J＝2.1Hz,J＝8.4Hz), 7.76(1H,dd,J＝0.6Hz,J＝2.1Hz),8.33(1H,dd,J＝0.9Hz,J＝1.8Hz)。
Synthesis example 2
Synthesis of 4- (5- ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) thio) -2-methylphenyl) -5-hydroxy-2, 6-dimethylpyridazin-3 (2H) -one (Compound No.1-2 described later)
4- (5- ((3-chloro-5- (trifluoromethyl) pyridin-2-yl) thio) -2-methylphenyl) -5-methoxy-2, 6-dimethylpyridazin-3 (2H) -one (122mg) was dissolved in morpholine (2ml) and the tube was sealed, followed by reaction at 140 ℃ for 50 minutes under microwave irradiation. After completion of the reaction, excess morpholine was distilled off, and acetic acid was added to the residue to make it acidic, and then the aqueous layer was extracted 2 times with ethyl acetate (10 ml). The organic layer was dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by column chromatography (heptane: ethyl acetate ═ 1: 1), whereby the objective substance was obtained as a white solid (51mg, yield 43%). The melting point of this material was 99-102 ℃ and the NMR spectrum data were as follows.
1H NMR(300MHz,CDCl3):δppm＝2.24(3H,s),2.30(3H,s),3.73(3H, s),7.36-7.48(3H,m),7.79(1H,d,J＝1.8Hz),8.32(1H,dd,J＝0.9Hz,J＝ 1.8Hz)。
Next, representative examples of the compounds of the present invention are shown in tables 1 to 3. These compounds can be synthesized based on the above-mentioned synthesis examples or production methods. In tables 1 to 3, No. represents Compound No. Me, ethylPr is an n-propyl group, i-Pr is an isopropyl group, n-Bu is an n-butyl group, t-Bu is a tert-butyl group, c-Pr is a cyclopropyl group, c-Hex is a cyclohexyl group, Ph is a phenyl group, and Bn is a benzyl group. In addition, "2, 6- (Me) in the Table2"represents that the methyl group is substituted at the 2-position and the 6-position, respectively, and the same shall apply to the other descriptions.
The values in the physical property columns of tables 1 to 3 are melting points (. degree. C.), and the compounds described as NMR are shown in Table 41H-NMR spectroscopic data.
[ Table 1]
Table 1
Figure BDA0001815266310000331
No. R1 R2 R3 R4 X Physical Properties
1-1 Me Me 6-Me H O 102-105
1-2 Me Me 6-Me H S 99-102
1-3 Me Me 6-Et H O 94-96
1-4 Me Me 6-Et H S 109-111
1-5 Me Me 6-Pr H O
1-6 Me Me 6-i-Pr H O
1-7 Me Me 6-t-Bu H O
1-8 Me Me 6-CF3 H O
1-9 Me Me 6-c-Pr H O
1-10 Me Me 6-OMe H O 133
1-11 Me Me 6-Cl H O
1-12 Me Me 2-Me H O 190
1-13 Me Me 2，6-(Me)2 H O 90
1-14 Me Me 4，6-(Me)2 H O 94
1-15 Me Me 4-Me H O
1-16 Me Me 6-Pr H S
1-17 Me Me 6-i-Pr H S
1-18 Me Me 6-t-Bu H S
1-19 Me Me 6-CF3 H S
1-20 Me Me 6-c-Pr H S
1-21 Me Me 6-OMe H S
1-22 Me Me 6-Cl H S
1-23 Me Me 2-Me H S
1～24 Me Me 2，6-(Me)2 H S
1-25 Me Me 4，6-(Me)2 H S
1-26 Me Me 4-Me H S
1-27 Me Me 6-Me Me O NMR
1-28 Me Me 6-Et Me O NMR
129 Me Me 2-Me Me O NMR
1-30 Me Me 6-Pr Me O
1-31 Me Me 6-i-Pr Me O
1-32 Me Me 6-Me Me S NMR
[ Table 2]
Watch 1 (continuation)
Figure BDA0001815266310000341
[ Table 3]
Watch 1 (continuation)
Figure BDA0001815266310000351
[ Table 4]
Watch 1 (continue)
Figure BDA0001815266310000361
[ Table 5]
Watch 1 (continuation)
Figure BDA0001815266310000371
[ Table 6]
Watch 1 (continuation)
Figure BDA0001815266310000381
[ Table 7]
Table 2
Figure BDA0001815266310000391
Figure BDA0001815266310000392
[ Table 8]
Watch 2 (continuation)
Figure BDA0001815266310000401
[ Table 9]
Watch 2 (continue)
Figure BDA0001815266310000411
[ Table 10]
Watch 2 (continuation)
Figure BDA0001815266310000421
[ Table 11]
Watch 2 (continuation)
Figure BDA0001815266310000431
[ Table 12]
Watch 2 (continuation)
Figure BDA0001815266310000441
[ Table 13]
Watch 2 (continuation)
Figure BDA0001815266310000451
[ Table 14]
Watch 2 (continuation)
Figure BDA0001815266310000461
[ Table 15]
Watch 2 (continue)
Figure BDA0001815266310000471
[ Table 16]
Watch 2 (continuation)
Figure BDA0001815266310000481
[ Table 17]
Watch 2 (continuation)
Figure BDA0001815266310000491
[ Table 18]
Watch 2 (continue)
Figure BDA0001815266310000501
[ Table 19]
Watch 2 (continuation)
Figure BDA0001815266310000511
[ Table 20]
No. 3 table
Figure BDA0001815266310000521
No. R1 R2 R3 R4 X Physical Properties
3-1 Me Me 6-Me H O 202-204
3-2 Me Me 6-Me H S
3-3 Me Me 6-Et H O
3-4 Me Me 6-Et H S
3-5 Me Me 6-Pr H O
3-6 Me Me 6-i-Pr H O
3-7 Me Me 6-t-Bu H O
3-8 Me Me 6-CF3 H O
3-9 Me Me 6-c-Pr H O
3-10 Me Me 6-OMe H O
3-11 Me Me 6-Cl H O
3-12 Me Me 2-Me H O
3-13 Me Me 2，6-(Me)2 H O
3-14 Me Me 4，6-(Me)2 H O
3-15 Me Me 4-Me H O
3-16 Me Me 6-Pr H S
3-17 Me Me 6-i-Pr H S
3-18 Me Me 6-t-Bu H S
3-19 Me Me 6-CF3 H S
3-20 Me Me 6-c-Pr H S
3-21 Me Me 6-OMe H S
3-22 Me Me 6-Cl H S
3-23 Me Me 2-Me H S
3-24 Me Me 2，6-(Me)2 H S
3-25 Me Me 4，6-(Me)2 H S
3-26 Me Me 4-Me H S
3-27 Me Me 6-Me Me O NMR
3-28 Me Me 6-Et Me O
3-29 Me Me 2-Me Me O
3-30 Me Me 6-Pr Me O
3-31 Me Me 6-i-Pr Me O
3-32 Me Me 6-Me Me S
[ Table 21]
Watch 3 (continuation)
Figure BDA0001815266310000531
[ Table 22]
Watch 3 (continuation)
Figure BDA0001815266310000541
[ Table 23]
Watch 3 (continue)
Figure BDA0001815266310000551
[ Table 24]
4 th table
Figure BDA0001815266310000561
[ Table 25]
Watch 4 (continue)
Figure BDA0001815266310000571
[ Table 26]
Watch 4 (continue)
Figure BDA0001815266310000581
[ Table 27]
Watch 4 (continue)
Figure BDA0001815266310000591
[ Table 28]
Watch 4 (continue)
Figure BDA0001815266310000601
[ Table 29]
Watch 4 (continue)
Figure BDA0001815266310000611
[ Table 30]
Watch 4 (continue)
Figure BDA0001815266310000621
[ Table 31]
Watch 4 (continue)
Figure BDA0001815266310000631
[ Table 32]
Watch 4 (continue)
Figure BDA0001815266310000641
[ Table 33]
Watch 4 (continue)
Figure BDA0001815266310000651
[ Table 34]
Watch 4 (continue)
Figure BDA0001815266310000661
[ Table 35]
Watch 4 (continue)
Figure BDA0001815266310000671
Next, test examples of the present invention are described.
Test example 1
Dry field crop soil was filled in 1/300,000 hectare pots, and seeds of various plants were sown. Then, the plants reached a certain age ((1) barnyard grass (barnyardgrass: (1))Echinochloa crus-galliL.))); 0.5-2.9 leaf stage, (2) crabgrass (crabgrass: (Digitaria sanguinalisL.))); 0.5-3.0 leaf stage, (3) green foxtail (green foxtail: (B))Setaria viridisL.))); 0.5-3.2 leaf stage, (4) wild oat (wild oat: (1)Avena fatuaL.)); 0.4-1.2 leaf stage, (5) Lolium multiflorum (italian ryegrass: (1))Lolium multiflorumLam.)); 0.4-2.0 leaf stage, (6) Amaranthus retroflexus (redroot pigweedAmaranthus retroflexusL.)); cotyledon-2.2 leaf stage, (7) rice (rice)(Oryza sativaL.))); 0.2-2.7 leaf stage, (8) corn (corn: (1)Zea maysL.))); 1.7-3.6 leaf stage, (9) wheat (wheat: (1:)Triticum aestivumL.))); 1.3-2.3 leaf stage, (10) soybean (soybean: (Glycine maxMerr.); first leaf stage), a wettable powder or emulsion prepared by a usual formulation method of the compound of the present invention is weighed so as to be a predetermined amount of active ingredient, and diluted to 0.1 vol% of water (containing an agricultural spreader (サーファクタント WK: pellets and バイオケミカル co.) corresponding to 1000 liters per 1 hectare. The prepared liquid was applied to stem and leaf treatment with a small-sized sprayer.
After the treatment with the agent, the growth state of each plant was visually observed on day 14, and the herbicidal effect was evaluated at growth inhibition (%) of 0 (equivalent to no treatment area) to 100 (complete withering), and the results of table 5 were obtained.
[ Table 36]
5 th table
Figure BDA0001815266310000681
[ Table 37]
Watch 5 (continuation)
Figure BDA0001815266310000691
[ Table 38]
Watch 5 (continuation)
Figure BDA0001815266310000701
[ Table 39]
Watch 5 (continuation)
Figure BDA0001815266310000711
[ Table 40]
Watch 5 (continuation)
Figure BDA0001815266310000721
[ Table 41]
Watch 5 (continuation)
Figure BDA0001815266310000731
Test example 2
The dry crop soil was filled in a pot of 1/300,000 hectares, and various plants were sown ((barnyardgrass: (barnyardgrass) ((barnyardgrass)Echinochloa crus-galliL.), and the rising crabgrass (crabgrass, (b.Digitaria sanguinalisL.), green foxtail (green foxtail:))Setaria viridisL.), Amaranthus retroflexus (retro pigweed: (Amaranthus retroflexus)Amaranthus retroflexusL.), Sida acuta (privclly sida) (a mixture ofSida spinosaL.), Abutilon (velvetleak: (L.))Abutilon theophrastiMEDIC), rice (rice)oryza sativaL.), corn (corn: (corn))Zea maysL.), wheat (wheat: (wheat) ((wheat))Triticum aestivumL.), soybean (soybean: (L.))Glycine maxMerr.)) from a seed. On the next day of sowing, a wettable powder or emulsion prepared by a conventional formulation method using the compound of the present invention was weighed to a predetermined amount of active ingredient, diluted to 1000 liters per 1 hectare of water, and soil treated with a small-sized sprayer.
After the treatment with the agent, the growth state of each plant was visually observed on day 14, and the herbicidal effect was evaluated at growth inhibition (%) rates of 0 (equivalent to no treatment zone) to 100 (complete withering), and the results of table 6 were obtained.
[ Table 42]
6 th table
Figure BDA0001815266310000741
[ Table 43]
Watch 6 (continue)
Figure BDA0001815266310000751
[ Table 44]
Watch 6 (continue)
Figure BDA0001815266310000761
[ Table 45]
Watch 6 (continue)
Figure RE-GDA0003597589200000011
Next, formulation examples of the present invention are described.
Preparation example 1
Figure RE-GDA0003597589200000012
The above components (1) to (4) were put into a high-speed mixing and granulating machine, and 20% water was further added thereto to granulate and dry the resulting mixture, thereby obtaining water-dispersible granules.
Preparation example 2
Figure RE-GDA0003597589200000013
Figure RE-GDA0003597589200000021
The mixture of the above components (1) to (4) is mixed with the compound of the present invention in a ratio of 9: 1 to obtain a wettable powder.
Preparation example 3
Figure RE-GDA0003597589200000022
The wettable powder is obtained by mixing the above components (1) to (4).
Preparation example 4
Figure RE-GDA0003597589200000023
Mixing the pre-pulverized (1) with (2) and (3), adding (4), (5) and water, mixing, and extruding for granulation. Then, the granules were obtained by drying and size-adjusting.
Preparation example 5
Figure RE-GDA0003597589200000024
Figure RE-GDA0003597589200000031
Mixing the above (1), (2) and (3), passing through a pulverizer, adding (4), kneading, and extruding for granulation. Then, the resulting granules were dried and granulated to obtain water-dispersible granules.
Preparation example 6
Figure RE-GDA0003597589200000032
The aqueous suspension is obtained by mixing the above components (1) to (6) and pulverizing the mixture using a wet pulverizer (denudator).
The present invention is not limited to the above embodiments, and various modifications can be made within the scope shown in the claims, and embodiments obtained by appropriately combining technical means disclosed in different embodiments are also included in the technical scope of the present invention. Further, by combining the technical means disclosed in the respective embodiments, new technical features can be formed.
Industrial applicability
The compound of the present invention can achieve a significant improvement in herbicidal activity against undesired plants, as compared with similar conventional compounds. In addition, it has high safety to crops. Accordingly, the pyridazinone compound or the salt thereof according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. The application range of the method relates to various fields such as agricultural lands such as paddy fields, dry lands, fruit tree gardens and mulberry gardens, non-agricultural lands such as mountain forests, field roads, sports grounds and workplace covers, and the application method can also be selected from soil treatment, stem leaf treatment, water treatment and the like.
In addition, the entire contents of the specification, claims, drawings and abstract of japanese patent application 2016-.

Claims (7)

1. A pyridazinone compound represented by the general formula (I) or a salt thereof,
Figure FDA0003597589190000011
in the formula (I), the compound is shown in the specification,
x is-O-, -S-or-N (Y) -;
q is phenyl which may have Z substituent, and is selected from thienyl, furyl, pyrrolyl, and the like which may have Z substituent,
Figure FDA0003597589190000012
Azolyl radical, iso
Figure FDA0003597589190000013
Azolyl radical, iso
Figure FDA0003597589190000014
Azolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazoleBase, 1,3,4-
Figure FDA0003597589190000015
Oxadiazolyl, 1,2,4-
Figure FDA0003597589190000016
A monocyclic heteroaryl group selected from a oxadiazolyl group, a 1,3, 4-thiadiazolyl group, a 1,2, 4-triazolyl group, a 1,2, 3-thiadiazolyl group, a 1,2,3, 4-tetrazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a 1,3, 5-triazinyl group, a 1,2, 4-triazinyl group, an imidazolinyl group, an imidazolidinyl group, a pyrazolinyl group and a pyrazolidinyl group, or a monocyclic heteroaryl group which may have a Z substituent selected from a benzothiophenyl group, a benzofuranyl group, an indolyl group, a benzothiazolyl group, a benzimidazolyl group, a benzisoxazolyl group
Figure FDA0003597589190000017
Azolyl, benzisothiazolyl, indazolyl, benzo
Figure FDA0003597589190000018
Oxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, naphthyridinyl, pyridopyrimidinyl, pyridopyrazinyl, imidazopyridinyl, thiazolopyridyl, pyrazolopyrimidyl, imidazopyrazinyl, imidazopyridazinyl, triazolopyridinyl, pyrazinyl, pyrazinopyridazinyl, pyrimidopyridazinyl, pyrimidopyrimidinyl, pyridopyridazinyl, pyrrolopyridinyl, thienopyridinyl, pyrrolopyridinyl, and the like,
Figure FDA0003597589190000019
Azolopyridinyl, pyrazolopyridinyl, iso-pyridinyl
Figure FDA00035975891900000110
Azolopyridinyl, isothiazolopyridinyl, pyrrolopyrimidinyl, thienopyrimidinyl, imidazopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl,
Figure FDA00035975891900000111
oxazolopyrimidinyl, thiazolopyrimidinyl, iso
Figure FDA00035975891900000112
Oxazolopyrimidinyl, isothiazolopyrimidinyl, pyrrolopyrazinyl, thienopyrazinyl, thiazolopyrimidinyl, pyrrolopyrazinyl, and pyrazolopyrimidyl, and pyrazolopyrimidinyl,
Figure FDA0003597589190000021
Azolopyrazinyl, thiazolopyrazinyl, pyrazolopyrazinyl, iso-pyrazinyl, thiazolopyrazinyl, pyrazolopyrazinyl, and pyrazolopyrazinyl
Figure FDA0003597589190000022
Azolopyrazinyl, isothiazolopyrazinyl, pyrrolopyridazinyl, thienopyridazinyl, pyrrolopyrazinyl, isothiazolopyridazinyl, pyrrolopyridazinyl, pyrrolopyrazinyl, thiazolopyridazinyl, and thiazolopyridazinyl,
Figure FDA0003597589190000023
Azolopyridazinyl, thiazolopyridazinyl, pyrazolopyridazinyl, isoxazinyl
Figure FDA0003597589190000024
Bicyclic heteroaryl of oxazolopyridazinyl, isothiazolopyridazinyl, purinyl and pteridinyl;
y is a hydrogen atom or C1-C12An alkyl group;
R1is C1-C12Alkyl radical, C2-C6Alkenyl radical, C3-C7Cycloalkyl radical C1-C12Alkyl, halo C1-C12Alkyl or C1-C12Alkyl carbonyl radical C1-C12An alkyl group;
R2is a hydrogen atom, C1-C12Alkyl or halo C1-C12An alkyl group;
R3is C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy or C3-C7A cycloalkyl group;
R4is a hydrogen atom, -C (O) R6、-C(S)R6、-SO2R7Phenyl which may have Z substituent, C1-C12Alkoxy radical C1-C12Alkyl, -CH (J)1)OCOOJ2、C2-C6Alkenyl radical, C1-C12Alkoxy radical C1-C12Alkoxy radical C1-C12Alkyl radical, C2-C6Alkynyl, cyano C1-C12Alkyl or halo C1-C12Alkoxy radical C1-C12An alkyl group;
R6is C1-C12Alkyl radical, C1-C12Alkoxy, morpholino, di-C1-C12Alkylamino, (phenyl) (C)1-C12Alkyl) amino, C3-C7Cycloalkyl radical, C1-C12Alkoxy radical C1-C12Alkyl radical, C1-C12Alkylthio group C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkylthio radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C12Alkoxycarbonyl radical C1-C12Alkyl radical, C3-C7Cycloalkyl radical C1-C12Alkyl, phenyl which may have Z substituent, and a substituent which may have Z substituent selected from the group consisting of thienyl, furyl, pyrrolyl, and the like,
Figure FDA0003597589190000025
Azolyl radical, iso
Figure FDA0003597589190000026
Azolyl radical, iso
Figure FDA0003597589190000027
Oxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-
Figure FDA0003597589190000028
Diazolyl, 1,2,4-
Figure FDA0003597589190000029
A monocyclic heteroaryl group selected from the group consisting of oxadiazolyl, 1,3, 4-thiadiazolyl, 1,2, 4-triazolyl, 1,2, 3-thiadiazolyl, 1,2,3, 4-tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, imidazolinyl, imidazolidinyl, pyrazolinyl and pyrazolidinyl, a phenylC which may have a Z substituent1-C12Alkyl, phenoxy which may have Z substituent, phenylthio which may have Z substituent, phenoxy C which may have Z substituent1-C12Alkyl radical, C1-C12Alkoxycarbonyl radical, C1-C12Alkoxy radical C1-C12Alkoxy, halo C1-C12Alkoxy radical, C2-C6Alkynyloxy, C2-C6Alkenyloxy or halogeno C2-C6An alkenyl group;
R7is C1-C12Alkyl, halo C1-C12Alkyl radical, C3-C7Cycloalkyl or phenyl which may have a Z substituent;
z is halogen, C1-C12Alkyl, halo C1-C12Alkyl radical, C1-C12Alkoxy or cyano;
J1is C1-C12An alkyl group;
J2is C1-C12Alkyl or C3-C7A cycloalkyl group;
n is an integer of 0 to 4.
2. The pyridazinone compound or the salt thereof according to claim 1, wherein in the general formula (I),
x is-O-, -S-or-N (Y) -;
q is phenyl which may have Z substituent, and is selected from thienyl, furyl, pyrrolyl, and the like which may have Z substituent,
Figure FDA0003597589190000031
Azolyl radical, iso
Figure FDA0003597589190000032
Azolyl radical, iso
Figure FDA0003597589190000033
Oxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-
Figure FDA0003597589190000034
Oxadiazolyl, 1,2,4-
Figure FDA0003597589190000035
A monocyclic heteroaryl group selected from the group consisting of a oxadiazolyl group, a 1,3, 4-thiadiazolyl group, a 1,2, 4-triazolyl group, a 1,2, 3-thiadiazolyl group, a 1,2,3, 4-tetrazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a 1,3, 5-triazinyl group, a 1,2, 4-triazinyl group, an imidazolinyl group, an imidazolidinyl group, a pyrazolinyl group and a pyrazolidinyl group, or a group selected from the group consisting of a benzothienyl group, a benzofuranyl group, an indolyl group, a benzothiazolyl group, a benzimidazolyl group, a benzisoxazolyl group, a 1,2, 4-thiadiazolyl group, a 1,2, 4-triazolyl group, a 1,2, 3-triazolyl group, a pyrimidinyl group, a pyridazinyl group, a 1, a pyridazinyl group, a pyrazolinyl group and a pyrazolidinyl group which may have a Z substituent
Figure FDA0003597589190000036
Azolyl, benzisothiazolyl, indazolyl, benzoazolyl
Figure FDA0003597589190000037
Oxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, naphthyridinyl, pyridopyrimidinyl, pyridopyrazinyl, imidazopyridinyl, thiazolopyridyl, pyrazolopyrimidyl, imidazopyrazinyl, imidazopyridazinyl, triazolopyridinyl, pyrazinyl, pyrazinopyridazinyl, pyrimidopyridazinyl, pyrimidopyrimidinyl, pyridopyridazinyl, pyrrolopyridinyl, thienopyridinyl, pyrrolopyridinyl, and the like,
Figure FDA0003597589190000038
Azolopyridinyl, pyrazolopyridinyl, iso-pyridinyl
Figure FDA0003597589190000039
Azolopyridinyl, isothiazolopyridinyl, pyrrolopyrimidinyl, thienopyrimidinyl, imidazopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, and pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl, thiazolinyl, pyrazolopyrimidinyl,
Figure FDA00035975891900000310
oxazolopyrimidinyl, thiazolopyrimidinyl, iso
Figure FDA00035975891900000311
Oxazolopyrimidinyl, isothiazolopyrimidinyl, pyrrolopyrazinyl, thienopyrazinyl, pyrazolopyrimidinyl, thiazolopyrimidinyl, and thiazolopyrimidinyl,
Figure FDA00035975891900000312
Azolopyrazinyl, thiazolopyrazinyl, pyrazolopyrazinyl, iso-pyrazinyl, thiazolopyrazinyl, pyrazolopyrazinyl, and pyrazolopyrazinyl
Figure FDA00035975891900000313
Azolopyrazinyl, isothiazolopyrazinyl, pyrrolopyridazinyl, thienopyridazinyl, pyrrolopyrazinyl, isothiazolopyridazinyl, pyrrolopyridazinyl, pyrrolopyrazinyl, thiazolopyridazinyl, and thiazolopyridazinyl,
Figure FDA00035975891900000314
Azolopyridazinyl, thiazolopyridazinyl, pyrazolopyridazinyl, isoxazinyl
Figure FDA00035975891900000315
Bicyclic heteroaryl of oxazolopyridazinyl, isothiazolopyridazinyl, purinyl and pteridinyl;
y is a hydrogen atom or C1-C12An alkyl group;
z is halogen, C1-C12Alkyl, halo C1-C12Alkyl or cyano;
R1is C1-C12Alkyl or C2-C6An alkenyl group;
R2is a hydrogen atom, C1-C12Alkyl or halogenGeneration C1-C12An alkyl group;
R3is C1-C12Alkyl radical, C1-C12Alkoxy, halo C1-C12Alkoxy or C3-C7A cycloalkyl group;
R4is a hydrogen atom, -C (O) R6or-SO2R7；
R6Is C1-C12Alkyl radical, C1-C12Alkoxy or morpholino;
R7is C1-C12An alkyl group;
n is an integer of 1 to 4.
3. The pyridazinone-based compound or salt thereof according to claim 1 or 2, wherein in the general formula (I),
q is phenyl, pyridyl, pyrimidinyl, pyrazinyl, benzothiazolyl, benzo
Figure FDA0003597589190000041
Oxazolyl, quinolinyl, quinoxalinyl or quinazolinyl.
4. The pyridazinone-based compound or salt thereof according to claim 1 or 2, wherein in the general formula (I),
x is-O-;
q is pyridyl or benzo which may have Z substituent
Figure FDA0003597589190000042
(ii) an azole group or a quinoxaline group,
z is halogen or halogeno C1-C12An alkyl group;
R1is C1-C12An alkyl group;
R2is C1-C12An alkyl group;
R3is C1-C12An alkyl group;
R4is a hydrogen atom;
n is an integer of 1 to 4.
5. A herbicide containing the pyridazinone compound or the salt thereof according to claim 1 or 2 as an active ingredient.
6. A method for controlling undesired plants or inhibiting their growth, which comprises applying a herbicidally effective amount of the pyridazinone compound or the salt thereof according to claim 1 or 2 to the undesired plants or to a locus where they grow, to control the undesired plants or inhibit their growth.
7. The method according to claim 6, wherein the pyridazinone compound or the salt thereof is applied in an amount of 0.1 to 5,000 g/ha.
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